2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86734727, compound

HRID 1834962Notes

Reaction equation

HRID 1834962 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[C:6]([OH:10])(=[O:9])[CH2:7][CH3:8].[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:32])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[C:6]([OH:10])(=[O:9])[CH2:7][CH3:8].[OH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:29]([CH2:30][CH2:31][C@:13]12[CH3:14])[C@:26]1([CH2:27][OH:28])[C:21](=[CH:22][C:23](=[O:32])[CH:24]=[CH:25]1)[CH2:20][CH2:19]3

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86734728HCID 86734728, compound

Product 1

HCID 86734727HCID 86734727, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

17β,19-Dihydroxy-4-androsten-3-one dipropionate and dichlorodicyanobenzoquinone are refluxed in anhydrous dioxane for about 48 hours. The mixture is cooled and filtered. The filtrate is concentrated under vacuum, methylenechloride is added and the mixture filtered. The filtrate is washed well with water, dried over sodium sulfate and the solvent removed. Chromatography of the residue on silica gel and eluting with methylenechloride yields an eluate. Removal of the solvent results in a solid which is crystallized from an acetone-hexane solution to yield the desired 17β,19-dihydroxy-1,4-androstadien-3-one dipropionate.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under vacuum, methylenechloride
  4. additionis added
  5. filtrationthe mixture filtered
  6. washThe filtrate is washed well with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent removed
  9. washChromatography of the residue on silica gel and eluting with methylenechloride
  10. customyields an eluate
  11. customRemoval of the solvent
  12. customresults in a solid which
  13. customis crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-ea71333796cf4524a4c392475f293678
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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